Potassium Hydroxide → 2-Benzyl-malonic acid monoethyl ester

HRID 1978211Notes

Reaction equation

HRID 1978211 reaction equation
[CH2:1]([O:3][C:4](=[O:18])[CH:5]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]([O:8]CC)=[O:7])[CH3:2].[OH-].[K+]>C(O)C>[CH2:1]([O:3][C:4](=[O:18])[CH:5]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]([OH:8])=[O:7])[CH3:2]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 69090Diethyl 2-benzylpropanedioate

Product 1

HCID 28848672-Benzyl-malonic acid monoethyl esterYield 90.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Benzylmalonic acid diethyl ester (10 g, 40 mmol) in 25 mL of ethanol is cooled to 0° C. Potassium hydroxide (2.5 g, 40 mmol) dissolved in 25 mL of ethanol is added dropwise over 50 minutes. The cooling bath is removed and the mixture is stirred for one additional hour. The volume of solvent is reduced by evaporation in vacuo, and the residual solution is poured into aqueous sodium bicarbonate solution and extracted twice with ethyl acetate. The aqueous phase is acidified with aqueous 10% HCl and extracted twice with ethyl acetate. The organic phase is dried with a brine extraction, filtered from anhydrous sodium sulfate, and concentrated in vacuo, yielding 8.08 g of the title compound as a colorless oil.

Workup

  1. additionis added dropwise over 50 minutes
  2. customThe cooling bath is removed
  3. customThe volume of solvent is reduced by evaporation in vacuo
  4. additionthe residual solution is poured into aqueous sodium bicarbonate solution
  5. extractionextracted twice with ethyl acetate
  6. extractionextracted twice with ethyl acetate
  7. dry with materialThe organic phase is dried with a brine extraction
  8. filtrationfiltered from anhydrous sodium sulfate
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f90e97ab42ae4b2495ef54292e0b05b1
Source dataset
uspto-grants-2001_05
Patent number
US06235928B1

Reaction notes

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